Triethylamine → HCID 123625959, compound

Participants

Reaction Steps

To a solution of tert-butyl(1-(4-(7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (50 mg, 0.11 mmol) in dry DCM (1 ml) was added triethyl amine (46 μl, 0.33 mmol) and methanesulfonyl chloride (26 μl, 0.33 mmol) under nitrogen. The resulting mixture was stirred for 1 hour at room temperature. A saturated solution of NaHCO3 was added and the mixture was extracted with dichloromethane (3×10 ml) using a phase separator (Isolute® SPE). The combined organic phases were concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 50% EtOAc in cyclohexane) to give the title compound (45 mg, 77%). 1H NMR (500 MHz, CDCl3): 8.00 (1H, s), 7.25 (2H, d), 7.19-7.17 (5H, m), 7.11-7.10 (2H, m), 4.95 (1H, s), 4.43 (2H, t), 3.90 (2H, t), 2.55-2.25 (7H, m), 2.06-1.98 (1H, m), 1.82-1.73 (1H, m), 1.44-1.15 (9H, br).

Provenance & Evidence